2-(2H-Benzotriazol-2-yl)-6-[(dicyclo­hexyl­amino)­meth­yl]-4-(2,4,4-trimethyl­pentan-2-yl)phenol

Chen, M.-J.; Wu, B.-H.; Li, C.-Y.; Lin, C.-H.; Ko, B.-T.

doi:10.1107/S1600536812038962

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2944

https://doi.org/10.1107/S1600536812038962

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2-(2H-Benzotriazol-2-yl)-6-[(dicyclohexylamino)methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol

Ming-Jen Chen,^a Ban-Hsin Wu,^b Chen-Yu Li,^b Chia-Her Lin ^b and Bao-Tsan Ko ^b ^*

^aDepartment of Applied Cosmetology and Graduate Institute of Cosmetic Science, Hungkuang University, Taichung City 443, Taiwan, and ^bDepartment of Chemistry, Chung Yuan Christian University, Chung-Li 320, Taiwan
^*Correspondence e-mail: btko@cycu.edu.tw

(Received 5 September 2012; accepted 12 September 2012; online 19 September 2012)

In the title molecule, C₃₃H₄₈N₄O, the dihedral angle between the mean planes of the benzotriazole ring system [maximun deviation = 0.038 (2) Å] and the phenol ring is 16.6 (2)°. There is an intramolecular O—H⋯N hydrogen bond between the phenol and benzotriazole groups.

Related literature

For background information and potential applications of the title compound, see: Chmura et al. (2006 ); Gendler et al. (2006 ); Li et al. (2011 ). For a related structure: see: Li et al. (2009 ).

Experimental

Crystal data

C₃₃H₄₈N₄O
M_r = 516.75
Monoclinic, P 2₁
a = 11.9975 (2) Å
b = 9.9620 (2) Å
c = 12.7511 (2) Å
β = 94.468 (1)°
V = 1519.37 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.52 × 0.45 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.968, T_max = 0.981
13765 measured reflections
6650 independent reflections
5895 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.01
6650 reflections
347 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0A⋯N1	0.85	1.88	2.618 (2)	145

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038962/lh5530sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038962/lh5530Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038962/lh5530Isup3.cml

checkCIF report

Comment top

Over the past decade, there has been considerable attention drawn to the development of amine-phenolate titanium alkoxides, due mainly to their applications in polymer preparations of well defined polyesters such as poly(ε-caprolactone) (PCL) and poly(lactide) (PLA) (Chmura et al., 2006 & Gendler et al., 2006). Such amine-phenolate type ligands can be easily synthesized via a Mannich condensation from a secondary (or primary) amine, paraformaldehyde, and 2, 4-di-substitute-phenol under reflux conditions. For instance, our group has successfully synthesized and structural characterized amine-phenolate ligands derived from benzotriazole phenoxide (BTP) ligands, and zinc complexes bearing such ligands have been demonstrated to catalyze the ε-caprolactone and β-butyrolactone polymerizations with good catalytic activities in a controlled fashion (Li et al., 2011). However, no amino-BTP ligand with sterically bulky pendant arm has been isolated to date. Herein, we present the synthesis and crystal structure of the title compound, (I), a potential ligand for the preparations of group 4 complexes.

The molecular structure of (I) is composed of a benzotriazole-phenol moiety and the dicyclohexylamino functionalized group (Fig. 1). The dihedral angle between the mean planes of the benzotriazole unit (maximun deviation 0.038 (2)Å for C12) and the benzene ring of the phenoxy group is 16.6 (2)°. There is an intramolecular O—H···N hydrogen bond between the phenol and benzotriazole groups (Table 1). The distance of N1···H is substantially shorter than the van der Waals distance of 2.75 Å for the N and H distance. It is interesting to note that the six-membered ring (O/C1/C2/N2/N1/H0A) formed from the O—H···N hydrogen-bond is almost planar with a mean deviation of 0.041 (2) Å. The bond distances of benzotriazol-phenolate group are similar to those found in the crystal structure of 2-(2H-benzotriazol-2-yl)-6-((diethylamino)methyl)-4-methylphenol (Li et al., 2009).

Related literature top

For background information and potential applications of the title compound, see: Chmura et al. (2006); Gendler et al. (2006); Li et al. (2011). For a related structure: see: Li et al. (2009).

Experimental top

The title compound was synthesized by the following procedure (Fig. 2): To a mixture of paraformaldehyde (1.20 g, 40.0 mmol) and dicyclohexylamine (8 ml, 40.0 mmol) was added 2-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol (3.23 g, 10.0 mmol). The resulting mixture was heated at 383K for 1 day and then dried under reduced pressure to yield the oily residue. The residue was separated by chromatography over silica gel and eluted with hexane/ethyl acetate (95/5) to afford 4.38 g of the title compound in 85% yield. Colorless crystals were obtained from the saturated hexane solution.

Structure description top

For background information and potential applications of the title compound, see: Chmura et al. (2006); Gendler et al. (2006); Li et al. (2011). For a related structure: see: Li et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The synthetic procedure.

2-(2H-Benzotriazol-2-yl)-6-[(dicyclohexylamino)methyl]-4-(2,4,4- trimethylpentan-2-yl)phenol top

Crystal data top

C₃₃H₄₈N₄O	F(000) = 564
M_r = 516.75	D_x = 1.130 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9957 reflections
a = 11.9975 (2) Å	θ = 2.4–28.2°
b = 9.9620 (2) Å	µ = 0.07 mm⁻¹
c = 12.7511 (2) Å	T = 296 K
β = 94.468 (1)°	Columnar, yellow
V = 1519.37 (5) Å³	0.52 × 0.45 × 0.23 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	6650 independent reflections
Radiation source: fine-focus sealed tube	5895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 1.7°
φ and ω scans	h = −15→13
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −13→13
T_min = 0.968, T_max = 0.981	l = −17→11
13765 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.060P)² + 0.080P] where P = (F_o² + 2F_c²)/3
6650 reflections	(Δ/σ)_max < 0.001
347 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₃₃H₄₈N₄O	V = 1519.37 (5) Å³
M_r = 516.75	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.9975 (2) Å	µ = 0.07 mm⁻¹
b = 9.9620 (2) Å	T = 296 K
c = 12.7511 (2) Å	0.52 × 0.45 × 0.23 mm
β = 94.468 (1)°

Data collection top

Bruker APEXII CCD diffractometer	6650 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	5895 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.981	R_int = 0.015
13765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.101	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
6650 reflections	Δρ_min = −0.15 e Å⁻³
347 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O	0.53426 (8)	0.35702 (10)	0.14005 (8)	0.0496 (3)
H0A	0.5588	0.2840	0.1162	0.074*
N1	0.68618 (9)	0.17687 (12)	0.10591 (9)	0.0443 (3)
N2	0.76242 (9)	0.26671 (11)	0.14046 (8)	0.0395 (2)
N3	0.86727 (9)	0.24269 (13)	0.11847 (10)	0.0484 (3)
N4	0.45573 (9)	0.71136 (12)	0.29380 (9)	0.0432 (3)
C1	0.62072 (10)	0.42880 (13)	0.18658 (10)	0.0380 (3)
C2	0.73240 (11)	0.38923 (13)	0.19034 (10)	0.0380 (3)
C3	0.81709 (11)	0.46880 (15)	0.23714 (11)	0.0424 (3)
H3B	0.8907	0.4389	0.2393	0.051*
C4	0.79395 (11)	0.59171 (14)	0.28062 (11)	0.0430 (3)
C5	0.68100 (11)	0.63126 (15)	0.27571 (11)	0.0438 (3)
H5A	0.6633	0.7138	0.3041	0.053*
C6	0.59560 (11)	0.55311 (14)	0.23071 (10)	0.0410 (3)
C7	0.74579 (12)	0.08412 (14)	0.05639 (11)	0.0432 (3)
C8	0.71115 (15)	−0.03181 (16)	0.00004 (13)	0.0550 (4)
H8A	0.6372	−0.0605	−0.0043	0.066*
C9	0.79132 (17)	−0.10002 (18)	−0.04794 (15)	0.0666 (5)
H9A	0.7710	−0.1761	−0.0871	0.080*
C10	0.90369 (18)	−0.05918 (18)	−0.04017 (16)	0.0738 (5)
H10A	0.9555	−0.1097	−0.0738	0.089*
C11	0.93929 (16)	0.05155 (18)	0.01481 (16)	0.0672 (5)
H11A	1.0140	0.0775	0.0196	0.081*
C12	0.85784 (12)	0.12549 (15)	0.06446 (12)	0.0463 (3)
C13	0.88502 (12)	0.68861 (16)	0.32557 (12)	0.0504 (3)
C14	0.8818 (2)	0.8105 (2)	0.25089 (16)	0.0819 (6)
H14A	0.8926	0.7808	0.1808	0.123*
H14B	0.9402	0.8722	0.2739	0.123*
H14C	0.8107	0.8545	0.2515	0.123*
C15	1.00213 (14)	0.6252 (2)	0.32593 (18)	0.0790 (6)
H15A	1.0171	0.6020	0.2553	0.118*
H15B	1.0051	0.5458	0.3687	0.118*
H15C	1.0572	0.6883	0.3540	0.118*
C16	0.86199 (12)	0.74430 (14)	0.43540 (12)	0.0464 (3)
H16A	0.9112	0.8209	0.4478	0.056*
H16B	0.7864	0.7796	0.4286	0.056*
C17	0.87178 (14)	0.66127 (16)	0.53714 (13)	0.0556 (4)
C18	0.8127 (2)	0.5252 (2)	0.52482 (16)	0.0873 (7)
H18A	0.7361	0.5387	0.4994	0.131*
H18B	0.8157	0.4806	0.5917	0.131*
H18C	0.8494	0.4710	0.4756	0.131*
C19	0.99370 (19)	0.6403 (3)	0.5801 (2)	0.0942 (7)
H19A	0.9956	0.5880	0.6435	0.141*
H19B	1.0282	0.7258	0.5950	0.141*
H19C	1.0336	0.5938	0.5287	0.141*
C20	0.81634 (19)	0.7435 (2)	0.62047 (15)	0.0792 (6)
H20A	0.7380	0.7530	0.6001	0.119*
H20B	0.8504	0.8306	0.6265	0.119*
H20C	0.8259	0.6982	0.6870	0.119*
C21	0.47483 (12)	0.60067 (16)	0.22229 (13)	0.0498 (4)
H21A	0.4545	0.6293	0.1506	0.060*
H21B	0.4267	0.5262	0.2377	0.060*
C22	0.43782 (12)	0.66512 (14)	0.40017 (11)	0.0444 (3)
H22A	0.4835	0.5841	0.4118	0.053*
C23	0.48267 (14)	0.76647 (17)	0.48255 (12)	0.0549 (4)
H23A	0.4405	0.8493	0.4736	0.066*
H23B	0.5602	0.7862	0.4720	0.066*
C24	0.47455 (17)	0.7143 (2)	0.59412 (13)	0.0689 (5)
H24A	0.5231	0.6370	0.6057	0.083*
H24B	0.4999	0.7833	0.6441	0.083*
C25	0.35640 (17)	0.6751 (2)	0.61270 (15)	0.0741 (5)
H25A	0.3094	0.7544	0.6091	0.089*
H25B	0.3548	0.6370	0.6826	0.089*
C26	0.31068 (16)	0.57374 (19)	0.53183 (16)	0.0701 (5)
H26A	0.3524	0.4906	0.5410	0.084*
H26B	0.2332	0.5548	0.5429	0.084*
C27	0.31846 (12)	0.62495 (17)	0.42101 (13)	0.0544 (4)
H27A	0.2697	0.7021	0.4095	0.065*
H27B	0.2927	0.5556	0.3715	0.065*
C28	0.38601 (11)	0.82172 (14)	0.24991 (11)	0.0434 (3)
H28A	0.3660	0.8762	0.3096	0.052*
C29	0.45310 (15)	0.91286 (19)	0.18167 (14)	0.0638 (4)
H29A	0.5201	0.9429	0.2225	0.077*
H29B	0.4761	0.8619	0.1222	0.077*
C30	0.3865 (2)	1.0342 (2)	0.14153 (18)	0.0806 (6)
H30A	0.3721	1.0917	0.2004	0.097*
H30B	0.4301	1.0851	0.0944	0.097*
C31	0.27623 (18)	0.9943 (2)	0.08383 (16)	0.0752 (5)
H31A	0.2334	1.0744	0.0648	0.090*
H31B	0.2906	0.9477	0.0195	0.090*
C32	0.20860 (15)	0.90448 (19)	0.15035 (14)	0.0635 (4)
H32A	0.1413	0.8759	0.1093	0.076*
H32C	0.1864	0.9546	0.2105	0.076*
C33	0.27546 (13)	0.78174 (17)	0.18845 (13)	0.0530 (4)
H33B	0.2915	0.7271	0.1285	0.064*
H33A	0.2312	0.7282	0.2334	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0346 (5)	0.0511 (6)	0.0625 (6)	0.0022 (4)	−0.0005 (4)	−0.0172 (5)
N1	0.0402 (6)	0.0436 (6)	0.0494 (6)	−0.0006 (5)	0.0055 (5)	−0.0046 (5)
N2	0.0327 (5)	0.0423 (6)	0.0438 (6)	0.0033 (5)	0.0057 (4)	−0.0005 (5)
N3	0.0350 (6)	0.0490 (7)	0.0619 (7)	0.0069 (5)	0.0089 (5)	−0.0011 (6)
N4	0.0367 (6)	0.0482 (6)	0.0443 (6)	0.0061 (5)	0.0012 (5)	−0.0095 (5)
C1	0.0322 (6)	0.0442 (7)	0.0377 (6)	0.0002 (5)	0.0037 (5)	−0.0015 (6)
C2	0.0363 (7)	0.0394 (7)	0.0391 (6)	0.0018 (5)	0.0077 (5)	−0.0010 (5)
C3	0.0310 (7)	0.0488 (7)	0.0478 (7)	−0.0004 (6)	0.0059 (5)	−0.0002 (6)
C4	0.0349 (7)	0.0479 (7)	0.0467 (7)	−0.0058 (6)	0.0063 (5)	−0.0035 (6)
C5	0.0381 (7)	0.0444 (7)	0.0492 (7)	0.0012 (6)	0.0058 (6)	−0.0064 (6)
C6	0.0348 (7)	0.0474 (7)	0.0412 (7)	0.0029 (6)	0.0047 (5)	−0.0040 (6)
C7	0.0457 (8)	0.0416 (7)	0.0423 (7)	0.0084 (6)	0.0037 (5)	0.0053 (6)
C8	0.0618 (10)	0.0441 (8)	0.0586 (9)	0.0047 (7)	0.0012 (7)	−0.0016 (7)
C9	0.0850 (13)	0.0465 (8)	0.0688 (10)	0.0142 (8)	0.0094 (9)	−0.0072 (8)
C10	0.0837 (14)	0.0572 (10)	0.0840 (12)	0.0267 (10)	0.0286 (10)	−0.0049 (9)
C11	0.0533 (9)	0.0593 (10)	0.0910 (13)	0.0170 (8)	0.0196 (9)	−0.0030 (9)
C12	0.0434 (8)	0.0434 (7)	0.0528 (7)	0.0109 (6)	0.0080 (6)	0.0041 (6)
C13	0.0394 (7)	0.0523 (8)	0.0600 (8)	−0.0118 (6)	0.0063 (6)	−0.0060 (7)
C14	0.0947 (15)	0.0814 (13)	0.0695 (11)	−0.0406 (12)	0.0063 (10)	0.0114 (10)
C15	0.0348 (8)	0.0998 (15)	0.1037 (15)	−0.0157 (9)	0.0139 (9)	−0.0395 (13)
C16	0.0410 (7)	0.0370 (7)	0.0602 (8)	−0.0040 (6)	−0.0017 (6)	−0.0023 (6)
C17	0.0585 (9)	0.0461 (8)	0.0609 (9)	−0.0024 (7)	−0.0027 (7)	0.0011 (7)
C18	0.135 (2)	0.0608 (11)	0.0662 (12)	−0.0351 (12)	0.0065 (12)	0.0075 (9)
C19	0.0854 (15)	0.0958 (16)	0.0957 (15)	0.0206 (13)	−0.0294 (12)	0.0083 (14)
C20	0.0955 (15)	0.0829 (13)	0.0591 (10)	−0.0009 (12)	0.0053 (10)	−0.0073 (10)
C21	0.0364 (7)	0.0554 (9)	0.0570 (8)	0.0070 (6)	−0.0011 (6)	−0.0177 (7)
C22	0.0397 (7)	0.0423 (7)	0.0511 (7)	0.0031 (6)	0.0032 (6)	−0.0042 (6)
C23	0.0589 (9)	0.0560 (9)	0.0491 (8)	−0.0063 (7)	0.0001 (6)	−0.0058 (7)
C24	0.0842 (13)	0.0750 (12)	0.0471 (8)	0.0031 (10)	0.0031 (8)	−0.0055 (8)
C25	0.0908 (14)	0.0731 (12)	0.0619 (10)	0.0196 (11)	0.0284 (9)	0.0063 (10)
C26	0.0639 (11)	0.0576 (10)	0.0926 (14)	0.0064 (8)	0.0303 (10)	0.0143 (10)
C27	0.0420 (8)	0.0504 (8)	0.0717 (10)	−0.0007 (7)	0.0100 (7)	−0.0044 (8)
C28	0.0408 (7)	0.0453 (7)	0.0440 (7)	0.0028 (6)	0.0037 (5)	−0.0075 (6)
C29	0.0575 (10)	0.0680 (10)	0.0654 (10)	−0.0119 (8)	0.0015 (8)	0.0047 (9)
C30	0.0976 (15)	0.0610 (11)	0.0804 (13)	−0.0151 (10)	−0.0113 (11)	0.0129 (10)
C31	0.0965 (15)	0.0628 (11)	0.0628 (11)	0.0076 (10)	−0.0159 (10)	0.0063 (9)
C32	0.0579 (10)	0.0692 (10)	0.0612 (9)	0.0192 (8)	−0.0101 (7)	−0.0075 (8)
C33	0.0438 (8)	0.0550 (9)	0.0590 (8)	0.0043 (7)	−0.0032 (6)	−0.0037 (7)

Geometric parameters (Å, º) top

O—C1	1.3577 (15)	C18—H18A	0.9600
O—H0A	0.8501	C18—H18B	0.9600
N1—N2	1.3300 (16)	C18—H18C	0.9600
N1—C7	1.3544 (18)	C19—H19A	0.9600
N2—N3	1.3317 (15)	C19—H19B	0.9600
N2—C2	1.4352 (17)	C19—H19C	0.9600
N3—C12	1.356 (2)	C20—H20A	0.9600
N4—C21	1.4603 (18)	C20—H20B	0.9600
N4—C22	1.4640 (19)	C20—H20C	0.9600
N4—C28	1.4658 (17)	C21—H21A	0.9700
C1—C2	1.3940 (18)	C21—H21B	0.9700
C1—C6	1.4027 (18)	C22—C23	1.525 (2)
C2—C3	1.3865 (18)	C22—C27	1.530 (2)
C3—C4	1.381 (2)	C22—H22A	0.9800
C3—H3B	0.9300	C23—C24	1.525 (2)
C4—C5	1.4080 (19)	C23—H23A	0.9700
C4—C13	1.5351 (19)	C23—H23B	0.9700
C5—C6	1.3760 (19)	C24—C25	1.507 (3)
C5—H5A	0.9300	C24—H24A	0.9700
C6—C21	1.5204 (19)	C24—H24B	0.9700
C7—C12	1.402 (2)	C25—C26	1.515 (3)
C7—C8	1.406 (2)	C25—H25A	0.9700
C8—C9	1.361 (2)	C25—H25B	0.9700
C8—H8A	0.9300	C26—C27	1.512 (3)
C9—C10	1.404 (3)	C26—H26A	0.9700
C9—H9A	0.9300	C26—H26B	0.9700
C10—C11	1.358 (3)	C27—H27A	0.9700
C10—H10A	0.9300	C27—H27B	0.9700
C11—C12	1.412 (2)	C28—C29	1.529 (2)
C11—H11A	0.9300	C28—C33	1.540 (2)
C13—C15	1.540 (2)	C28—H28A	0.9800
C13—C14	1.542 (3)	C29—C30	1.516 (3)
C13—C16	1.551 (2)	C29—H29A	0.9700
C14—H14A	0.9600	C29—H29B	0.9700
C14—H14B	0.9600	C30—C31	1.516 (3)
C14—H14C	0.9600	C30—H30A	0.9700
C15—H15A	0.9600	C30—H30B	0.9700
C15—H15B	0.9600	C31—C32	1.512 (3)
C15—H15C	0.9600	C31—H31A	0.9700
C16—C17	1.535 (2)	C31—H31B	0.9700
C16—H16A	0.9700	C32—C33	1.521 (2)
C16—H16B	0.9700	C32—H32A	0.9700
C17—C18	1.532 (3)	C32—H32C	0.9700
C17—C20	1.534 (3)	C33—H33B	0.9700
C17—C19	1.536 (3)	C33—H33A	0.9700

C1—O—H0A	109.5	H19B—C19—H19C	109.5
N2—N1—C7	103.83 (11)	C17—C20—H20A	109.5
N1—N2—N3	116.48 (11)	C17—C20—H20B	109.5
N1—N2—C2	121.96 (10)	H20A—C20—H20B	109.5
N3—N2—C2	121.32 (11)	C17—C20—H20C	109.5
N2—N3—C12	102.64 (12)	H20A—C20—H20C	109.5
C21—N4—C22	112.48 (12)	H20B—C20—H20C	109.5
C21—N4—C28	116.14 (11)	N4—C21—C6	112.72 (11)
C22—N4—C28	117.98 (10)	N4—C21—H21A	109.0
O—C1—C2	124.46 (11)	C6—C21—H21A	109.0
O—C1—C6	117.36 (11)	N4—C21—H21B	109.0
C2—C1—C6	118.15 (11)	C6—C21—H21B	109.0
C3—C2—C1	121.56 (12)	H21A—C21—H21B	107.8
C3—C2—N2	118.44 (11)	N4—C22—C23	111.13 (12)
C1—C2—N2	119.93 (11)	N4—C22—C27	116.75 (12)
C4—C3—C2	121.07 (12)	C23—C22—C27	109.78 (12)
C4—C3—H3B	119.5	N4—C22—H22A	106.2
C2—C3—H3B	119.5	C23—C22—H22A	106.2
C3—C4—C5	116.94 (12)	C27—C22—H22A	106.2
C3—C4—C13	123.22 (12)	C22—C23—C24	111.85 (14)
C5—C4—C13	119.69 (13)	C22—C23—H23A	109.2
C6—C5—C4	122.89 (13)	C24—C23—H23A	109.2
C6—C5—H5A	118.6	C22—C23—H23B	109.2
C4—C5—H5A	118.6	C24—C23—H23B	109.2
C5—C6—C1	119.38 (12)	H23A—C23—H23B	107.9
C5—C6—C21	121.85 (12)	C25—C24—C23	111.37 (15)
C1—C6—C21	118.69 (12)	C25—C24—H24A	109.4
N1—C7—C12	107.66 (12)	C23—C24—H24A	109.4
N1—C7—C8	130.77 (14)	C25—C24—H24B	109.4
C12—C7—C8	121.50 (14)	C23—C24—H24B	109.4
C9—C8—C7	116.66 (17)	H24A—C24—H24B	108.0
C9—C8—H8A	121.7	C24—C25—C26	111.16 (14)
C7—C8—H8A	121.7	C24—C25—H25A	109.4
C8—C9—C10	122.13 (18)	C26—C25—H25A	109.4
C8—C9—H9A	118.9	C24—C25—H25B	109.4
C10—C9—H9A	118.9	C26—C25—H25B	109.4
C11—C10—C9	122.23 (16)	H25A—C25—H25B	108.0
C11—C10—H10A	118.9	C27—C26—C25	111.46 (15)
C9—C10—H10A	118.9	C27—C26—H26A	109.3
C10—C11—C12	117.02 (18)	C25—C26—H26A	109.3
C10—C11—H11A	121.5	C27—C26—H26B	109.3
C12—C11—H11A	121.5	C25—C26—H26B	109.3
N3—C12—C7	109.39 (12)	H26A—C26—H26B	108.0
N3—C12—C11	130.06 (15)	C26—C27—C22	112.17 (14)
C7—C12—C11	120.44 (15)	C26—C27—H27A	109.2
C4—C13—C15	111.46 (13)	C22—C27—H27A	109.2
C4—C13—C14	106.38 (13)	C26—C27—H27B	109.2
C15—C13—C14	107.68 (15)	C22—C27—H27B	109.2
C4—C13—C16	112.98 (11)	H27A—C27—H27B	107.9
C15—C13—C16	111.75 (13)	N4—C28—C29	110.65 (12)
C14—C13—C16	106.16 (14)	N4—C28—C33	116.33 (12)
C13—C14—H14A	109.5	C29—C28—C33	109.55 (13)
C13—C14—H14B	109.5	N4—C28—H28A	106.6
H14A—C14—H14B	109.5	C29—C28—H28A	106.6
C13—C14—H14C	109.5	C33—C28—H28A	106.6
H14A—C14—H14C	109.5	C30—C29—C28	112.24 (16)
H14B—C14—H14C	109.5	C30—C29—H29A	109.2
C13—C15—H15A	109.5	C28—C29—H29A	109.2
C13—C15—H15B	109.5	C30—C29—H29B	109.2
H15A—C15—H15B	109.5	C28—C29—H29B	109.2
C13—C15—H15C	109.5	H29A—C29—H29B	107.9
H15A—C15—H15C	109.5	C31—C30—C29	111.81 (16)
H15B—C15—H15C	109.5	C31—C30—H30A	109.3
C17—C16—C13	124.26 (13)	C29—C30—H30A	109.3
C17—C16—H16A	106.3	C31—C30—H30B	109.3
C13—C16—H16A	106.3	C29—C30—H30B	109.3
C17—C16—H16B	106.3	H30A—C30—H30B	107.9
C13—C16—H16B	106.3	C32—C31—C30	111.67 (16)
H16A—C16—H16B	106.4	C32—C31—H31A	109.3
C18—C17—C20	108.75 (17)	C30—C31—H31A	109.3
C18—C17—C16	112.69 (14)	C32—C31—H31B	109.3
C20—C17—C16	106.80 (14)	C30—C31—H31B	109.3
C18—C17—C19	109.63 (19)	H31A—C31—H31B	107.9
C20—C17—C19	106.13 (17)	C31—C32—C33	111.23 (16)
C16—C17—C19	112.52 (16)	C31—C32—H32A	109.4
C17—C18—H18A	109.5	C33—C32—H32A	109.4
C17—C18—H18B	109.5	C31—C32—H32C	109.4
H18A—C18—H18B	109.5	C33—C32—H32C	109.4
C17—C18—H18C	109.5	H32A—C32—H32C	108.0
H18A—C18—H18C	109.5	C32—C33—C28	111.50 (14)
H18B—C18—H18C	109.5	C32—C33—H33B	109.3
C17—C19—H19A	109.5	C28—C33—H33B	109.3
C17—C19—H19B	109.5	C32—C33—H33A	109.3
H19A—C19—H19B	109.5	C28—C33—H33A	109.3
C17—C19—H19C	109.5	H33B—C33—H33A	108.0
H19A—C19—H19C	109.5

C7—N1—N2—N3	0.11 (15)	C5—C4—C13—C15	178.87 (15)
C7—N1—N2—C2	174.59 (11)	C3—C4—C13—C14	111.33 (17)
N1—N2—N3—C12	−0.10 (15)	C5—C4—C13—C14	−64.02 (18)
C2—N2—N3—C12	−174.62 (12)	C3—C4—C13—C16	−132.59 (14)
O—C1—C2—C3	178.53 (12)	C5—C4—C13—C16	52.06 (18)
C6—C1—C2—C3	0.68 (19)	C4—C13—C16—C17	71.79 (18)
O—C1—C2—N2	1.67 (19)	C15—C13—C16—C17	−54.9 (2)
C6—C1—C2—N2	−176.18 (12)	C14—C13—C16—C17	−171.99 (15)
N1—N2—C2—C3	171.18 (11)	C13—C16—C17—C18	−47.7 (2)
N3—N2—C2—C3	−14.61 (18)	C13—C16—C17—C20	−167.09 (15)
N1—N2—C2—C1	−11.86 (18)	C13—C16—C17—C19	76.8 (2)
N3—N2—C2—C1	162.35 (12)	C22—N4—C21—C6	−83.04 (16)
C1—C2—C3—C4	−0.9 (2)	C28—N4—C21—C6	136.72 (13)
N2—C2—C3—C4	175.96 (12)	C5—C6—C21—N4	−18.4 (2)
C2—C3—C4—C5	0.4 (2)	C1—C6—C21—N4	164.79 (12)
C2—C3—C4—C13	−175.04 (13)	C21—N4—C22—C23	147.68 (12)
C3—C4—C5—C6	0.3 (2)	C28—N4—C22—C23	−72.88 (15)
C13—C4—C5—C6	175.97 (13)	C21—N4—C22—C27	−85.37 (15)
C4—C5—C6—C1	−0.6 (2)	C28—N4—C22—C27	54.08 (17)
C4—C5—C6—C21	−177.38 (14)	N4—C22—C23—C24	−174.72 (13)
O—C1—C6—C5	−177.94 (12)	C27—C22—C23—C24	54.60 (18)
C2—C1—C6—C5	0.06 (19)	C22—C23—C24—C25	−55.9 (2)
O—C1—C6—C21	−1.03 (19)	C23—C24—C25—C26	55.4 (2)
C2—C1—C6—C21	176.97 (13)	C24—C25—C26—C27	−55.3 (2)
N2—N1—C7—C12	−0.07 (14)	C25—C26—C27—C22	55.49 (19)
N2—N1—C7—C8	−176.86 (14)	N4—C22—C27—C26	177.72 (13)
N1—C7—C8—C9	175.11 (15)	C23—C22—C27—C26	−54.66 (18)
C12—C7—C8—C9	−1.3 (2)	C21—N4—C28—C29	−77.80 (15)
C7—C8—C9—C10	1.3 (3)	C22—N4—C28—C29	144.21 (13)
C8—C9—C10—C11	−0.6 (3)	C21—N4—C28—C33	48.05 (17)
C9—C10—C11—C12	−0.2 (3)	C22—N4—C28—C33	−89.95 (15)
N2—N3—C12—C7	0.05 (14)	N4—C28—C29—C30	−175.64 (13)
N2—N3—C12—C11	176.20 (17)	C33—C28—C29—C30	54.80 (18)
N1—C7—C12—N3	0.01 (16)	C28—C29—C30—C31	−54.6 (2)
C8—C7—C12—N3	177.16 (13)	C29—C30—C31—C32	54.1 (2)
N1—C7—C12—C11	−176.58 (15)	C30—C31—C32—C33	−55.1 (2)
C8—C7—C12—C11	0.6 (2)	C31—C32—C33—C28	56.48 (19)
C10—C11—C12—N3	−175.62 (16)	N4—C28—C33—C32	177.89 (13)
C10—C11—C12—C7	0.2 (3)	C29—C28—C33—C32	−55.72 (18)
C3—C4—C13—C15	−5.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N1	0.85	1.88	2.618 (2)	145

Experimental details

Crystal data
Chemical formula	C₃₃H₄₈N₄O
M_r	516.75
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	11.9975 (2), 9.9620 (2), 12.7511 (2)
β (°)	94.468 (1)
V (Å³)	1519.37 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.52 × 0.45 × 0.23

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.968, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	13765, 6650, 5895
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.01
No. of reflections	6650
No. of parameters	347
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N1	0.85	1.877	2.618 (2)	144.9

Acknowledgements

We gratefully acknowledge the financial support in part from the National Science Council, Taiwan (NSC99–2119-M-241–001-MY2 and NSC101–2113-M-033–008-MY3).

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chmura, A. J., Davidson, M. G., Jones, M. D., Lunn, M. D., Mahon, M. F., Johnson, A. F., Khunkamchoo, P., Roberts, S. L. & Wong, S. S. F. (2006). Macromolecules, 39, 7250–7257. Web of Science CSD CrossRef CAS Google Scholar
Gendler, S., Segal, S., Goldberg, I., Goldschmidt, Z. & Kol, M. (2006). Inorg. Chem. 45, 4783–4790. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, J.-Y., Li, C.-Y., Tai, W.-J., Lin, C.-H. & Ko, B.-T. (2011). Inorg. Chem. Commun. 14, 1140–1144. Web of Science CSD CrossRef CAS Google Scholar
Li, J.-Y., Liu, Y.-C., Lin, C.-H. & Ko, B.-T. (2009). Acta Cryst. E65, o2475. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(2H-Benzotriazol-2-yl)-6-[(di­cyclo­hexyl­amino)­meth­yl]-4-(2,4,4-tri­methyl­pentan-2-yl)phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(2H-Benzotriazol-2-yl)-6-[(dicyclohexylamino)methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol